Compounds containing the diazeniumdiolate [N(O)═NO]− functional group have proven useful as research tools in a variety of applications requiring spontaneous release of nitric oxide (NO). Hrabie, J. A.; Keefer, L. K. Chem. Rev. 2002, 102, 1135-1154. Anions such as 1-(N,N-dialkylamino)diazen-1-ium-1,2-diolates 1 (where R is alkyl) are stable as solid salts, but release up to 2 mol of NO when dissolved in aqueous solution at physiologically relevant conditions.
These compounds have shown great potential in a variety of medical applications requiring either the rapid production or gradual release of NO (see, Keefer, L. K. Annu. Rev. Pharmacol. Toxicol. 2003, 43, 585-607; Saavedra, J. E.; Fitzhugh, A. L.; Keefer, L. K. Nitric Oxide and the Cardiovascular System 2000, 431-446), and have allowed biological consequences of NO delivery rates to be probed. Saavedra, J. E.; Fitzhugh, A. L.; Keefer, L. K. Nitric Oxide and the Cardiovascular System 2000, 431-446.
A major factor affecting decomposition rate is ease of protonation at the amine nitrogen leading to amine and 2 equivalents of NO:

It is now discovered that by making protonation at this site unfavorable, an alternate decomposition pathway to nitrosamine and nitroxyl (NOIHNO) becomes available as illustrated below:

This has implications in that nitroxyl is implicated in the treatment of disease, including cardiovascular system diseases and disorders. Accordingly, as there is a need in the field for effective therapies for treating cardiovascular disorders, particularly by delivery of nitroxyl, the compounds herein and methods of using them provide unique and novel therapeutic opportunities.